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Rozanne Gilmore forayed into politics, but ultimately foccused on her teaching career.<ref name=vp/> She began teaching at [[Randolph–Macon College]] beginning in 1983 as a part-time professor.<ref name=wpost/> She then worked as a Latin teacher at public high schools in [[Chesterfield County, Virginia|Chesterfield]] and [[Henrico County|Henrico]] counties before returning to Randolph-Macon.<ref name=vp/><ref name=wpost/>
Roxane Gilmore later became a [[classics]] professor at [[Randolph–Macon College]] in [[Ashland, Virginia]], where she taught [[Latin language|Latin]] and a range of courses, including [[History of
Upon becoming Virginia's first lady in 1998, Gilmore chose to actively continuing teaching at Randolph-Macon, becoming the first First Lady in state history to retain her own, independent career during her tenure.<ref name=wpost/><ref name=vp2>{{cite news |first=|last=|title=Virginia's New First Lady to Keep Her Day Job |url=https://www.pilotonline.com/1998/01/12/vas-new-first-lady-to-be-first-to-keep-day-job/ |work=[[The Virginia Pilot]] |publisher= |date=1998-01-12 |access-date=2024-09-02 |archive-url=https://web.archive.org/web/20240830090458/https://www.pilotonline.com/1998/01/12/vas-new-first-lady-to-be-first-to-keep-day-job/ |archive-date=2024-08-30 |url-status=live}}</ref> In a 1998 interview with the ''[[Washington Post]]'', [[Larry Sabato]] of the [[University of Virginia Center for Politics]], explained that, by keeping her career, Gilmore broke the mold for her predecessors at the time, "We've never had a [[first lady]] like Roxane Gilmore. This is a very traditional state. She's the first of a kind...In other places, even [[Arkansas]], this happened a long time ago...We've had some very good, very active first ladies like [[Jeannie Baliles]]. But their lives have always been defined by their husband's job. Roxane is the first with a completely independent identity."<ref name=wpost/> First Lady Roxane Gilmore oversaw the restoration of [[Executive Mansion (Virginia)|Virginia Governor's Mansion]], the longest continually occupied [[List of governors' residences in the United States|governor’s residence in the United States]].<ref name=vp/><ref name=wpost/> The mansion, built in 1813, was in need of repairs and restoration work when Governor Gilmore took office in 1998. Roxane Gilmore researched and toured dozens of homes across Virginia and the [[American South|South]] to gather ideas that could be used in the renovations, including [[Monticello]], [[Kenmore (Fredericksburg, Virginia)|Kenmore]], [[Wickham House]], and the [[John Marshall House]] in [[Richmond, Virginia]].<ref name=wpost/> Gilmore and her family moved out in April 1998 once construction began and returned to governor's residence in November 1999 following its $5 million renovation.<ref name=wpost/>
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